US4225733A - Method for hydrogenating an aromatic compound - Google Patents
Method for hydrogenating an aromatic compound Download PDFInfo
- Publication number
- US4225733A US4225733A US05/919,985 US91998578A US4225733A US 4225733 A US4225733 A US 4225733A US 91998578 A US91998578 A US 91998578A US 4225733 A US4225733 A US 4225733A
- Authority
- US
- United States
- Prior art keywords
- aromatic compound
- ruthenium
- hydrogen iodide
- amount
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims abstract description 13
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 8
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- VDRDGQXTSLSKKY-UHFFFAOYSA-K ruthenium(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[Ru+3] VDRDGQXTSLSKKY-UHFFFAOYSA-K 0.000 claims description 4
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims 4
- 229910001925 ruthenium oxide Inorganic materials 0.000 claims 2
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims 2
- 150000004996 alkyl benzenes Chemical class 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 150000003303 ruthenium Chemical class 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/10—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of aromatic six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/46—Ruthenium, rhodium, osmium or iridium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- the present invention relates to a method for hydrogenating an aromatic compound.
- the present inventors have tried to establish a method for producing hydrogen from hydrogen iodide and found an effective method in which hydrogen iodide is reacted with an aromatic compound at first and the obtained hydrogenated compound is dehydrogenated.
- An object of the present invention is to provide a novel method for hydrogenating an aromatic compound at a high yield close to the theoretical yield.
- the objects are achieved by a method for hydrogenating an aromatic compound, which comprises reacting the aromatic compound with hydrogen iodide in the presence of ruthenium catalyst.
- a novel catalyst used in the method of the present invention is ruthenium catalyst.
- Ruthenium may be used in any form, for example, ruthenium metal, its hydroxide, its oxide or its salt of organic acid or inorganic acid.
- the ruthenium catalyst may also be used together with a carrier, for example, barium sulfate, alumina, silica or aluminosilicate.
- Preparation of the catalyst may be easily carried out by a known method for preparing a catalyst of a metal like platinum, and generally no particular operation is required upon preparation.
- aromatic compound whatever aromatic compound capable of being subjected to a conventional hydrogenation reaction may be used.
- any compounds having one or more benzene nucleus may be used.
- aromatic compound having 6 to 16 carbon atoms may be preferably used.
- Typical examples of the aromatic compound include aromatic hydrocarbons such as benzene, toluene, xylene, trimethyl benzene, tetramethyl benzene, ethyl benzene, propyl benzene, diphenyl methane, naphthalene, methyl naphthalene, of which benzene and alkyl bnezene are especially preferable.
- An aromatic compound having one or more substituents inert to the hydrogenation reaction such as hydroxy group or alkoxy group, may also be used.
- the reaction temperature is preferably 25°-300° C., more preferably 25°-200° C.
- the reaction pressure is preferably 1-200 kg/cm 2 , more preferably 5-100 kg/cm 2
- the amount of hydrogen iodide to the aromatic compound is preferably 3-20 times by mole, more preferably 6-10 times by mole.
- the reaction of the present invention is preferably carried out in the presence of water. Coexistence of water brings hydrogen iodide to an aqueous layer and therefore make it easy to contact with the aromatic compound.
- the amount of water to hydrogen iodide is preferably 1-10 times by mole, more preferably 2-6 times by mole.
- the aromatic compound may be converted to the corresponding alicyclic compound at a high yield close to the theoretical yield.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Provided is a method for hydrogenating an aromatic compound by reacting the aromatic compound with hydrogen iodide in the presence of ruthenium catalyst.
Description
The present invention relates to a method for hydrogenating an aromatic compound.
Heretofore, there have been proposed many methods for the hydrogenation of aromatics. One of the most conventional methods is a catalytic reduction method using hydrogen gas. Such conventional method has disadvantages in economy and easiness to handle, and others.
Meanwhile, there has been known that in the case of producing hydrogen by using water and hydrogen sulfide as the raw material, iodine is used as a hydrogen acceptor and thereby hydrogen is recovered as hydrogen iodide (for example, H2 S+I2 →2HI+S, 2H2 O+2I2 →4HI+O2). In such method, it is very important that hydrogen is efficiently isolated and recovered from the obtained hydrogen iodide.
The present inventors have tried to establish a method for producing hydrogen from hydrogen iodide and found an effective method in which hydrogen iodide is reacted with an aromatic compound at first and the obtained hydrogenated compound is dehydrogenated.
An object of the present invention is to provide a novel method for hydrogenating an aromatic compound at a high yield close to the theoretical yield.
Other objects and advantages of the present invention will become clearer from considering the following description.
According to the present invention the objects are achieved by a method for hydrogenating an aromatic compound, which comprises reacting the aromatic compound with hydrogen iodide in the presence of ruthenium catalyst.
A novel catalyst used in the method of the present invention is ruthenium catalyst. Ruthenium may be used in any form, for example, ruthenium metal, its hydroxide, its oxide or its salt of organic acid or inorganic acid. The ruthenium catalyst may also be used together with a carrier, for example, barium sulfate, alumina, silica or aluminosilicate.
Preparation of the catalyst may be easily carried out by a known method for preparing a catalyst of a metal like platinum, and generally no particular operation is required upon preparation.
As a raw material aromatic compound whatever aromatic compound capable of being subjected to a conventional hydrogenation reaction may be used. In other words, any compounds having one or more benzene nucleus may be used. Usually, an aromatic compound having 6 to 16 carbon atoms may be preferably used. Typical examples of the aromatic compound include aromatic hydrocarbons such as benzene, toluene, xylene, trimethyl benzene, tetramethyl benzene, ethyl benzene, propyl benzene, diphenyl methane, naphthalene, methyl naphthalene, of which benzene and alkyl bnezene are especially preferable. An aromatic compound having one or more substituents inert to the hydrogenation reaction, such as hydroxy group or alkoxy group, may also be used.
In the method of the present invention, the reaction temperature is preferably 25°-300° C., more preferably 25°-200° C., the reaction pressure is preferably 1-200 kg/cm2, more preferably 5-100 kg/cm2, and the amount of hydrogen iodide to the aromatic compound is preferably 3-20 times by mole, more preferably 6-10 times by mole.
The reaction of the present invention is preferably carried out in the presence of water. Coexistence of water brings hydrogen iodide to an aqueous layer and therefore make it easy to contact with the aromatic compound. The amount of water to hydrogen iodide is preferably 1-10 times by mole, more preferably 2-6 times by mole.
According to the present invention, the aromatic compound may be converted to the corresponding alicyclic compound at a high yield close to the theoretical yield.
On the contrary, in the case of using nickel or platinum catalyst, which is a typical catalyst in the conventional catalytic reduction in place of ruthenium catalyst in the method of the present invention, the expected results cannot be achieved.
The present invention will now be explained in greater detail in conjunction with specific examples thereof.
Into an autoclave having an internal capacity of about 100 ml, 40 ml (HI: 3.03×10-1 mole) of an aqueous solution of hydrogen iodide (HI content being 57%, specific gravity being 1.7), 4.4 ml (4.95×10-2 mole) of benzene and 0.66 g of ruthenium hydroxide as a catalyst were charged, and a reaction was carried out under the conditions of 150° C. and 10 kg/cm2 for 2 hours by stirring. The yield of the produced cyclohexane to the used benzene was 100%.
Using 1 g of ruthenium supported on barium sulfate (ruthenium content 5% by weight), in place of ruthenium hydroxide in example 1, a reaction was carried out under the same conditions as in example 1, and the yield found of cyclohexane was 100%.
Using platinum net as a catalyst and a reaction temperature of 200° C., a reaction was carried out under the same conditions as in example 1, and the yield found of cyclohexane was only 5%.
Claims (6)
1. A method of hydrogenating an aromatic compound comprising: contacting an aromatic compound selected from the group consisting of benzene and alkyl benzene having 1 to 3 alkyl substituents at a temperature of from 25°to 300° C. under a reaction pressure within a range of 1-200 kg/cm2, with a catalytic amount of a catalyst selected from the group consisting of metal ruthenium, ruthenium hydroxide, ruthenium oxide and a ruthenium salt of an organic acid or inorganic acid, said catalyst being unsupported or supported on a carrier selected from the group consisting of barium sulfate and alumina, and a reducing agent consisting of hydrogen iodide, the amount of the hydrogen iodide being 3-20 times the amount of the aromatic compound, by mole, to completely hydrogenate the aromatic compound and produce an alicyclic compound corresponding to the aromatic compound in near theoretical yields and recovering the alicyclic compound.
2. The method according to claim 1, in which the hydrogenation reaction is carried out in the presence of water.
3. The method according to claim 2, in which the amount of water to hydrogen iodide is 1-10 times by mole.
4. The method according to claim 1 in which a catalytic amount of metal ruthenium is used.
5. The method according to claim 1 in which a catalytic amount of ruthenium hydroxide is used.
6. The method according to claim 1 in which a catalytic amount of ruthenium oxide is used.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52/81155 | 1977-07-07 | ||
| JP8115577A JPS5414939A (en) | 1977-07-07 | 1977-07-07 | Hydrogenation of aromatic compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4225733A true US4225733A (en) | 1980-09-30 |
Family
ID=13738538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/919,985 Expired - Lifetime US4225733A (en) | 1977-07-07 | 1978-06-28 | Method for hydrogenating an aromatic compound |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4225733A (en) |
| JP (1) | JPS5414939A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4495373A (en) * | 1983-02-24 | 1985-01-22 | Director-General Of The Agency Of Industrial Science And Technology | Method for partial nuclear hydrogenation of aromatic hydrocarbon compounds and a hydrogenation catalyst therefor |
| US4575572A (en) * | 1984-07-31 | 1986-03-11 | Sumitomo Chemical Company, Limited | Method for producing cycloolefins |
| US4665274A (en) * | 1985-09-11 | 1987-05-12 | Sumitomo Chemical Company, Limited | Method for producing cycloolefins |
| US20080139383A1 (en) * | 2006-03-27 | 2008-06-12 | Catalytic Distillation Technologies | Hydrogenation of aromatic compounds |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6195163B2 (en) * | 2014-02-13 | 2017-09-13 | 国立大学法人 千葉大学 | Method for alkylating ketones |
| JP7345777B2 (en) * | 2019-06-11 | 2023-09-19 | 国立大学法人千葉大学 | Method for producing ketone compounds, method for producing carboxylic acid derivatives |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3344200A (en) * | 1964-11-30 | 1967-09-26 | Shell Oil Co | Process for selective partial hydrogenation of polyaromatic compounds |
-
1977
- 1977-07-07 JP JP8115577A patent/JPS5414939A/en active Granted
-
1978
- 1978-06-28 US US05/919,985 patent/US4225733A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3344200A (en) * | 1964-11-30 | 1967-09-26 | Shell Oil Co | Process for selective partial hydrogenation of polyaromatic compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4495373A (en) * | 1983-02-24 | 1985-01-22 | Director-General Of The Agency Of Industrial Science And Technology | Method for partial nuclear hydrogenation of aromatic hydrocarbon compounds and a hydrogenation catalyst therefor |
| US4575572A (en) * | 1984-07-31 | 1986-03-11 | Sumitomo Chemical Company, Limited | Method for producing cycloolefins |
| US4665274A (en) * | 1985-09-11 | 1987-05-12 | Sumitomo Chemical Company, Limited | Method for producing cycloolefins |
| US20080139383A1 (en) * | 2006-03-27 | 2008-06-12 | Catalytic Distillation Technologies | Hydrogenation of aromatic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS563329B2 (en) | 1981-01-24 |
| JPS5414939A (en) | 1979-02-03 |
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